Substituted nitrogen-containing heterobicycles, the preparation thereof and their use as pharmaceutical compositions
Abstract
The present invention relates to new substituted nitrogen-containing heterobicyclic compounds of general formula wherein B, X 1 to X 3 and R 1 to R 5 are defined as in claim 1, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties. The compounds of the above general formula I as well as the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, and their stereoisomers have valuable pharmacological properties, particularly an antithrombotic activity and a factor Xa-inhibiting activity.
Claims
exact text as granted — not AI-modified1. A substituted nitrogen-containing heterobicyclic compound of formula
wherein
R 1 denotes a 2,5-dihydro-1H-pyrrol-1-yl-carbonyl, pyrrolidin-1-yl-carbonyl, 2-(aminomethyl)-pyrrolidin-1-yl-carbonyl, 2-(N-tert.-butyloxycarbonylaminomethyl)-pyrrolidin-1-yl-carbonyl, 3-oxo-piperazin-1-yl-carbonyl, morpholin-4-yl-carbonyl, carboxy, 3-aminomethyl-pyrrolidin-1-yl-carbonyl, thiazolidin-3-yl-carbonyl, 3-aminomethyl-pyrrolidin-1-yl-carbonyl, pyrazolidin-3-on-1-yl-carbonyl, pyrrolidin-2-ylmethylamino-carbonyl, 1-tert.-butyloxycarbonyl-pyrrolidin-2-yl-methylamino-carbonyl, 2-(acetylamino-methyl)-pyrrolidin-1-yl-carbonyl, 2-(pyrrolidin-1-yl-methyl)-pyrrolidin-1-yl-carbonyl, 2-(tert.-butyloxycarbonyl-aminomethyl)-thiazolidin-1-yl-carbonyl, 2-(pyridin-4-yl)-pyrrolidin-1-yl-carbonyl, 2-aminomethyl-thiazolidinyl-carbonyl, 2-(methanesulphonyl-aminomethyl)-pyrrolidin-1-yl-carbonyl, 2-acetaminomethyl-thiazolidin-1-yl-carbonyl, 5,6,7, 8-tetrahydro -[1,2,4]triazolo[4,3a]pyridin-4-yl, 2-(pyridin-4-yl)-thiazolidin-3-yl-carbonyl, 2-(2,2,2-trifluorethyl)-thiazolidin-3-yl-carbonyl, 2-(2-aminoethyl)-pyrrolidin-1-yl-carbonyl, 2-ethoxycarbonyl-piperidin-1-yl-carbonyl, 4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-5-yl-carbonyl, 2-benzhydryl-pyrrolidin-1-yl-carbonyl, [1,4]diazepan-1-yl-carbonyl, 2-(2-ethoxycarbonyl-ethyl)-piperidin-1-yl-carbonyl, 2-methylaminocarbonyl-pyrrolidin-1-yl-carbonyl, 3-(3-diethylamino-propyl)-piperidin-1-yl-carbonyl, 4-methyl-piperidin-1-yl-carbonyl, 2-(phenylaminomethyl)-pyrrolidin-1-yl-carbonyl, 2-benzyl-pyrrolidin-1-yl-carbonyl, 3-hydroxy-piperidin-1-yl-carbonyl, 2-dimethylaminocarbonyl-pyrrolidin-1-yl-carbonyl, piperidin-1-yl-carbonyl, 4-oxo-piperidin-1-yl-carbonyl, 4-methylene-piperidin-1-yl-carbonyl, 2-methyl-piperidin-1-yl-carbonyl, 2-benzyloxycarbonyl-pyrrolidin-1-yl-carbonyl, N-(3-amino-propyl)-N-ethyl-amino-carbonyl, N-cyclopropyl-N-methylamino-carbonyl, 2-methoxymethyl-pyrrolidin-1-yl-carbonyl, 3-(1H-benzimidazol-2-yl)-piperidin-1-yl]-carbonyl, 3-dimethylamino-pyrrolidin-1-yl-carbonyl, 2,5-dimethyl-2,5-dihydro-1H-pyrrol-1-yl)-carbonyl, 2-isopropyl-pyrrolidin-1-yl-carbonyl, 2-aminomethyl-piperidin-1-yl-carbonyl], 3-aminomethyl-piperidin-1-yl-carbonyl, 2-ethoxycarbonyl-pyrrolidin-1-yl-carbonyl, 3-(dimethylamino-methyl)-piperidin-1-yl-carbonyl, 2-(2-phenyl-ethyl)-pyrrolidin-1-yl-carbonyl, 2-(pyridin-2-yl)-pyrrolidin-1-yl-carbonyl, 2-(2-amino-ethyl)-piperidin-1-yl-carbonyl, 4-acetyl-piperazin-1-yl-carbonyl, N-(2-amino-ethyl)-N-ethyl-amino-carbonyl, 2-(pyridin-3-yl)-piperidin-1-yl-carbonyl, 2,5-dimethyl-pyrrolidin-1-yl-carbonyl, 4-aminocarbonyl-piperidin-1-yl-carbonyl, 4-hydroxy-piperidin-1-yl-carbonyl, 2-ethoxycarbonyl-piperidin-1-yl-carbonyl, 1-(1,4,6,7-tetrahydro-pyrazolo [4,3]pyridin-5-yl)-carbonyl, 2,5-dimethoxymethyl-pyrrolidin-1-yl-carbonyl, 2-methoxycarbonyl-pyrrolidin-1-yl-carbonyl, pyrazolidin-1-yl-carbonyl, 1-oxo-thiomorpholin-4-yl-carbonyl, 2-[(N-butyl-N-ethyl-amino)-methyl]-piperidin-1-yl-carbonyl, N-ethyl-N-(piperidin-4-yl)-aminocarbonyl, 4-formyl-piperazin-1-yl-carbonyl, 2-(2-dimethylamino-ethyl)-piperidin-1-yl-carbonyl, 2-(2-diethylamino-ethyl)-piperidin-1-yl-carbonyl, 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl-carbonyl, 3,6-dihydro-2H-pyridin-1-yl-carbonyl, 2-[(N-butyl-N-methyl-amino)-methyl]-piperidin-1-yl-carbonyl, 2-methyl-morpholin-4-yl-carbonyl, thiomorpholin-4-yl-carbonyl, 2-(2-amino-ethyl)-piperidin-1-yl-carbonyl, 2-ethyl-piperidin-1-yl-carbonyl, 3 -amino-pyrrolidin-1-yl-carbonyl, 4-trifluoromethyl-piperidin-1-yl-carbonyl, 3-[4-(pyrrolidin-1-yl)-butyl]-pyrrolidin-1-yl-carbonyl, 2-[(N-methyl-N-(pyridin-2-ylmethyl)-amino)-methyl]-piperidin-1-yl-carbonyl, 4-hydroxy-piperazin-1-yl-carbonyl, 3-(pyrrolidin-1-ylmethyl)-piperidin-1-yl-carbonyl, 2-diethylaminomethyl-piperidin-1-yl-carbonyl, 2-(4-diethylamino-butyl)-piperidin-1-yl-carbonyl, 2-hydroxymethyl-pyrrolidin-1-yl-carbonyl, 2-(N-ethyl-N-methyl-aminomethyl)-piperidin-1-yl-carbonyl, 2-aminocarbonyl-pyrrolidin-1-yl-carbonyl, 2-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl-carbonyl, 2-methoxymethyl-pyrrolidin-1-yl-carbonyl, 2-(3-dimethylamino-propyl)-piperidin-1-yl-carbonyl, 2-diethylaminocarbonyl-piperidin-1-yl-carbonyl, 2-[(N-cyclohexyl-N-methyl-amino)-methyl]-piperidin-1-yl-carbonyl, 2-piperidin-1-ylmethyl-piperidin-1-yl-carbonyl, 2-(1-methyl-1H-pyrazol-4-yl)-thiazolidinyl -carbonyl or 6,7,8,9-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-4-yl- group,
R 2 denotes a hydrogen, fluorine, chlorine or bromine atom, a C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2-3 -alkenyl, C 2-3 -alkynyl, nitro, amino, C 1-3 -alkoxy, a mono-, di- or trifluoromethoxy group,
R 3 denotes a hydrogen atom or a C 1-3 -alkyl group,
R 4 denotes a hydrogen atom, a methyl, propyl, 2-methylsuiphanyl-ethyl, 2-methylsuiphonyl-ethyl, hydroxymethyl, 2-carboxyethyl, 2-benzyloxycarbonyl-ethyl, 2-methoxy-ethyl, 2-methylsulphinyl-ethyl, tert.-butyloxycarbonylmethoxy-methyl, 2-ethoxycarbonyl-ethyl, carboxymethoxy-methyl, o-chlorophenyl, p-chlorophenyl, methoxymethyl, 2-diethyl -aminocarbonyl-ethyl, 2-propargyloxycarbonyl-ethyl, 2-(pyrrolidin-1-yl-carbonyl)-ethyl, 2-[N-methyl-N-piperidin-4-yl-amino]-carbonyl-ethyl, 2-[4-methyl-piperazin-1-yl]-carbonyl-ethyl, 2-(C-piperidin-4-yl-methylamino)-carbonyl-ethyl, 2-(N-benzyl-N-methyl-amino)-carbonyl-ethyl, 3 -tert.-butyloxycarbonyl-propyl, 2-benzyloxycarbonylamino-ethyl, 2-[(1,2,3,4-tetrahydroisoquinolin-1-yl)-carbonyl-ethyl, 2-(benzylamino-carbonyl)-ethyl, 2-[(N-methyl-N-phenethyl-amino-carbonyl)-ethyl, 2-(hydroxyethylamino-carbonyl)-ethyl, 2-[(C-pyridin-3-yl-methylamino-carbonyl)-propyl, 2-[(1-oxa-3,8-diaza-spiro[4.5]decan-2-on-8-yl)-carbonyl]-ethyl, 2-(morpholin-4-yl-carbonyl)-ethyl, 2-(C-cyclohexyl-methylamino-carbonyl)-ethyl, 2-(methoxyethylamino-carbonyl)-ethyl, 2-(dimethylaminoethyl-amino-carbonyl)-ethyl, 2-(cyclopropylamino-carbonyl)-ethyl, 2-[C-2-tetrahydrofuran-2-yl-methylamino-carbonyl)-ethyl, 2-(dimethylaminopropylamino-carbonyl)-ethyl, 2-(aminoethylamino-carbonyl)-ethyl, 2-(hydroxycarbonylmethyl-methyl-amino-carbonyl)-ethyl, 2-((3-(pyrrolidin-2-on-1-yl)-propyl)-amino-carbonyl)-ethyl, 2-[(1-[1,3,5]triazin-2-yl-piperidin-4-ylamino)-carbonyl]-ethyl, 2-[(2-imidazol-1-yl-ethylamino)-carbonyl)-ethyl, 2-[C-(1H-imidazol-2-yl)-methylamino-carbonyl)-ethyl, 2-(2,2,2-trifluoroethylamino-carbonyl)-ethyl, 2-[N-(2-dimethylamino-ethyl)-N-methyl-amino-carbonyl]-ethyl, 2-[1-phenyl-ethylamino-carbonyl]-ethyl, 2-[2-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl-carbonyl]-ethyl, 2-(N-aminocarbonylmethyl-N-methyl-amino-carbonyl)-ethyl, 2-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-5-yl-carbonyl)-ethyl, 2-(1-oxo-thiomorpholin-4-yl-carbonyl)-ethyl, 2-(N-dimethylaminocarbonylmethyl-N-methyl-amino-carbonyl)-ethyl, 2-(N -hydroxycarbonylethyl-N-methyl-amino-carbonyl)-ethyl, 2-[C-(1-methyl-1H-imidazol-2-yl)-methylamino-carbonyl)-ethyl, 2-(N-piperidin-2-yl-aminocarbonyl)-ethyl, 2-[C-(tetrahydropyran-4-yl)-methylamino-carbonyl]-ethyl, 2-(4-hydroxypiperidin-1-yl-carbonyl)-ethyl, 2-[C-(pyridin-4-yl)-methylamino-carbonyl]-ethyl, 2-(N-methylaminocarbonylmethyl-N-methyl-amino-carbonyl)-ethyl, 2-[N-(2-(1H)-imidazol-4-yl)-ethyl-N-methyl-amino-carbonyl]-ethyl, 2-(1-thiazolidin-3-yl-carbonyl)-ethyl, 2-(N-cyclopropyl-N-methyl-amino-carbonyl)-ethyl, 2-(cyclopentylamino-carbonyl)-ethyl, 2-(N-piperidin-4-yl-aminocarbonyl)-ethyl, 2-[C-(pyridin-2-yl)-methylamino-carbonyl]-ethyl, 2-(4-thiazol-2-yl-piperazin-1-yl-carbonyl)-ethyl, 2-(piperidin-1-yl-carbonyl)-ethyl, 2-amino-ethyl, thiophen-3-yl, 2-(2-oxo-pyrrolidin-1-yl)-ethyl, 2-(1,1-dioxo-isothiazolidin-2-yl)-ethyl, isopropylcarbonyloxy-methyl, 3-carboxy-propyl, 2-methylsulphonylamino-ethyl, methylsulphanyl-methyl, benzyloxy-methyl, 2-[2-(pyridin-4-yl-amino)-ethylamino-carbonyl]-ethyl, but-3-yn-1-yl, 1-methoxy-ethyl, 1-tert.-butyloxy-ethyl or 1-hydroxy-ethyl group,
R 5 denotes a hydrogen atom or a C 1-3 -alkyl group or
R 4 and R 5 together with the carbon atom to which they are bound denote a C 3-7 -cycloalky group, wherein
one of the methylene groups of the C 3-7 -cycloalkyl group may be replaced by an imino, C 1-3 -alkylimino, acylimino or suiphonylimino group,
B denotes a benzimidazole of the formula
wherein
n denotes the number 1 or 2, R 6 denotes a hydrogen atom or a C 1-3 -alkyl, hydroxy, amino, C 1-3 -alkylamino group, R 7 denotes a hydrogen, fluorine, chlorine or bromine atom, a C 1-3 -alkyl group wherein the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2-3 -alkenyl or C 2-3 -alkynyl, a hydroxy, C 1-3 -alkoxy, trifluoromethoxy or cyano group, and
X 1 and X 3 are N,
X 2 is a CH group optionally substituted by a C 1-3 -alkyl group,
unless otherwise stated the alkyl and alkoxy groups contained in the above definitions which have more than two carbon atoms may be straight-chain or branched and the alkyl groups in the above-mentioned dialkylated groups may be identical or different,
and the hydrogen atoms of the methyl or ethyl groups contained in the above-mentioned definitions may be wholly or partly replaced by fluorine atoms,
the tautomer, the diastereomer, the enantiomer, mixtures thereof and the salt thereof.
2. The compound of formula I according to claim 1 selected from the following compounds, or a tautomer, stereoisomer or salt thereof:
(2) 6-chloro-4-[C-(5-chloro-1H-benzimidazol-2-yl)-methylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(3) 4-[C-(5-chloro-1H-benzimidazol-2-yl)methylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(4) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(5) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl)-quinazoline,
(6) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2-aminomethyl-pyrrolidin-1-yl-carbonyl)-quinazoline,
(7) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(morpholin-4-yl-carbonyl)-quinazoline,
(8) 6-chloro-4-[1-(S)-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(piperazin-3-on-1-yl-carbonyl)-quinazoline,
(9) 6-chloro-4-[1-(S)-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(10) 6-chloro-4-[1-(S)-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(18) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(19) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R)-2-amino-methyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(20) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxy-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(21) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxy-ethylamino]-7-[(2R)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(22) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxy-ethylamino]-7-[(2R)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(23) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(24) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(25) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonylpropylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(26) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-benzyloxycarbonylpropylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(27) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-7-[(2R)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(28) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(29) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methoxy-propylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(30) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(31) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-7-[(2R)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(32) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphinyl-propylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(33) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-benzyloxycarbonylpropylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(34) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxy-ethylamino]-7-(piperazin-3-on-1-yl-carbonyl)-quinazoline,
(35) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphinyl-propylamino]-7-[(2R)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(36) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline,
(37) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(38) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-benzyloxycarbonylpropylamino]-7-[(2S)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(39) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonylpropyl-amino]-7-[(2S)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(40) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonylpropyl-amino]-7-[(2S)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(41) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-7-[(2R)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(42) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-7-[(2R)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(43) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(thiazolidin-3-yl-carbonyl)-quinazoline,
(44) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-(tert.-butyloxycarbonyl-methoxy)-ethylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(45) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-ethoxycarbonylpropylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(46) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(47) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-6-methyl-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(48) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3S)-3-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(49) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-(hydroxycarbonylmethoxy)-ethylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(50) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphinyl-propylamino]-7-[(2R)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(51) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-6-methyl-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(52) 6-bromo-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(53) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-ethoxycarbonylpropyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(54) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(pyrazolidin-3-on-1-yl-carbonyl)-quinazoline,
(55) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(56) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-1-(2-chloro-phenyl)-methylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(57) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-1-(3-chloro-phenyl)-methylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(58) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-butylamino]-7-(2,5-dihdropyrrol-1-yl-carbonyl)-quinazoline,
(59) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(60) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(61) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-diethylaminocarbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(62) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(pyrrolidin-1-ylcarbonyl)-propylamino]-7-[(2R)-pyrrolidin-2-ylmethylamino-carbonyl]-quinazoline,
(63) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-[N-methyl-N-piperidin-4-yl-amino]-carbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(64) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-[4-methyl-piperazin-1-yl]-carbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(65) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(C-piperidin-4-yl-methylamino)-carbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(66) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-benzyl-N-methyl-amino)-carbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(67) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-1-oxy-7-[(2R)-2-tert.-butyloxycarbonyl-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(68) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-allyloxycarbonylpropyl-amino]-6-methyl-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(69) 6-bromo-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-allyloxycarbonylpropyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(70) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(71) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-4-(tert.-butyloxycarbonyl)-butyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(72) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-4-(tert.-butyloxycarbonyl)-butyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(73) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-benzyloxycarbonyl-propylamino]-7-[(2R)-(1-tert.-butyloxycarbonyl-pyrrolidin-2-yl-methylamino)-carbonyl]-quinazoline,
(74) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-1-oxy-7-[(2R)-2-aminomethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(75) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R)-2-(acetylamino-methyl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(76) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-(pyrrolidin-1-yl-methyl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(77) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(tert.-butyloxycarbonyl-aminomethyl)-thiazolidin-1-yl-carbonyl]-quinazoline,
(78) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(pyridin-4-yl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(79) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-aminomethyl-thiazolidinyl-carbonyl]-quinazoline,
(80) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonyl-propylamino]-7-[(2R)-2-(methanesulphonyl-aminomethyl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(81) 6-chloro-4-[(1S)-3-(benzyloxycarbonyl-amino)-1-(5-chloro-1H-benzimidazol-2-yl)-propyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(82) 7-(2-acetaminomethyl-thiazolidin-1-yl-carbonyl)-6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-quinazoline,
(83) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[(1,2,3,4-tetrahydroisoquinolin-1-yl)-carbonyl-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(84) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(benzylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(85) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[(N-methyl-N-phenethyl-amino-carbonyl)-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(86) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(hydroxyethylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(87) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[(C-pyridin-3-yl-methylamino-carbonyl)-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(88) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[(1-oxa-3,8-diaza-spiro[4.5]decan-2-on-8-yl)-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(89) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(morpholin-4-yl-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(90) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(C-cyclohexyl-methylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(91) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(methoxyethylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(92) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(dimethylaminoethyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(93) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(cyclopropylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(94) 6-chloro-4-{(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-[C-(2R/S)-tetrahydrofuran-2-yl-methylamino-carbonyl)-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(95) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(dimethylaminopropylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(96) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(aminoethylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1 -yl-carbonyl)-quinazoline,
(97) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(hydroxycarbonylmethyl-methyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(98) 6-chloro-4-{[1-(5-chloro-1H-benzimidazol-2-yl)-3-((3-(pyrrolidin-2-on-1yl)-propyl)-amino-carbonyl)-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(99) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[(1-[1,3,5]triazin-2-yl-piperidin-4-ylamino)-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(100) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[(2-imidazol-1-yl-ethylamino)-carbonyl)-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(101) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[C-(1H-imidazol-2-yl)-methylamino-carbonyl)-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(102) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(2,2,2-trifluoroethylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(103) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[N-(2-dimethylamino-ethyl)-N-methyl-amino-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(104) 6-chloro-4-{(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-[(1R/S)-1-phenyl-ethylamino-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(105) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[2-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(106) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-aminocarbonylmethyl-N-methyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(107) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-5-yl-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(108) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(1-oxo-thiomorpholin-4-yl-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(109) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-dimethylaminocarbonylmethyl-N-methyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(110) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-hydroxycarbonylethyl-N-methyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(111) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[C-(1-methyl-1H-imidazol-2-yl)-methylamino-carbonyl)-propyl-amino]}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(112) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-piperidin-2-yl-aminocarbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(113) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[C-(tetrahydropyran-4-yl)-methylamino-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(114) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(4-hydroxypiperidin-1-yl-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(115) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[C-(pyridin-4-yl)-methylamino-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(116) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-methylaminocarbonylmethyl-N-methyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(117) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[N-(2-(1H)-imidazol-4-yl)-ethyl)-N-methyl-amino-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(118) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(1-thiazolidin-3-yl-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(119) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-cyclopropyl-N-methyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(120) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-cyclopropylmethyl-N-methyl-amino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(121) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(cyclopentylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(122) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(N-piperidin-4-yl-aminocarbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(123) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[C-(pyridin-2-yl)-methylamino-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(124) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(4-thiazol-2-yl-piperazin-1-yl-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(125) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(piperidin-1-yl-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(126) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-amino-propyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(127) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonyl-propylamino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline,
(128) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3a]pyridin-4-yl)-quinazoline,
(129) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-1-(thiophen-3-yl)-methylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(130) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(2-oxo-pyrrolidin-1-yl)-propyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(131) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(1,1-dioxo-isothiazolidin-2-yl)-propyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(132) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-isopropylcarbonyloxy-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(133) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-4 -(hydroxycarbonyl)-butylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(134) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(pyridin-4-yl)-thiazolidin-3-yl-carbonyl]-quinazoline,
(135) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(2,2,2-trifluorethyl)-thiazolidin-3-yl-carbonyl]-quinazoline,
(136) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methanesulphonylamino-propyl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(137) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methylsulphanyl-ethylamino]-7-(2, 5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(138) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-6-methoxy-quinazoline,
(139) 7-[(2S)-2-(2-aminoethyl)-pyrrolidin-1-yl-carbonyl]-6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-quinazoline,
(140) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-ethoxycarbonyl-piperidin-1-yl-carbonyl]-quinazoline,
(141) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-5-yl-carbonyl)-quinazoline,
(142) 7-[(2S)-2-benzhydryl-pyrrolidin-1-yl-carbonyl]-6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-quinazoline,
(143) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-([1,4]diazepan-1-yl-carbonyl)-quinazoline,
(144) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(2-ethoxycarbonyl-ethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(145) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-methylaminocarbonyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(146) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3R/S)-3-(3-diethylamino-propyl)-piperidin-1-yl-carbonyl]-quinazoline,
(147) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-methyl-piperidin-1-yl-carbonyl)-quinazoline,
(148) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-(phenylaminomethyl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(149) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-benzyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(150) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3R/S)-3-hydroxy-piperidin-1-yl-carbonyl]-quinazoline,
(151) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-dimethylaminocarbonyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(152) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(piperidin-1-yl-carbonyl)-quinazoline,
(153) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-oxo-piperidin-1-yl-carbonyl)-quinazoline,
(154) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-methylene-piperidin-1-yl-carbonyl)-quinazoline,
(155) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-methyl-piperidin-1-yl-carbonyl]-quinazoline,
(156) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-benzyloxycarbonyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(157) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[N-(3-amino-propyl)-N-ethyl-amino-carbonyl]-quinazoline,
(158) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(N-cyclopropyl-N-methylamino-carbonyl)-quinazoline,
(159) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2-oxo-piperazin-4-yl-carbonyl)-quinazoline,
(160) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-methoxymethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(161) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2)-2-(phenylaminomethyl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(162) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{1-[(3R/S)-3-(1H-benzimidazol-2-yl)-piperidin-1-yl]-carbonyl}-quinazoline,
(163) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3R/S)-3-dimethylamino-pyrrolidin-1-yl-carbonyl]-quinazoline,
(164) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2,5-dimethyl-2,5-dihydro-1H-pyrrol-1-yl)-carbonyl]-quinazoline,
(165) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-isopropyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(166) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-aminomethyl-piperidin-1-yl-carbonyl]-quinazoline,
(167) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3R/S)-3-aminomethyl-piperidin-1-yl-carbonyl]-quinazoline,
(168) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R)-2-ethoxycarbonyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(169) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[3-(dimethylamino-methyl)-piperidin-1-yl-carbonyl]-quinazoline,
(170) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(2-phenyl-ethyl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(171) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(pyridin-2-yl)-pyrrolidin-1-yl-carbonyl]-quinazoline,
(172) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(2-amino-ethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(173) 6-chloro-4-[l -(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-acetyl-piperazin-1-yl-carbonyl)-quinazoline,
(174) 6-chloro-4-[ 1 -(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[N-(2-amino-ethyl)-N-ethyl-amino-carbonyl]-quinazoline,
(175) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(pyridin-3-yl)-piperidin-1-yl-carbonyl]-quinazoline,
(176) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S),(5R/S)-2,5-dimethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(177) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-aminocarbonyl-piperidin-1-yl-carbonyl)-quinazoline,
(178) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-hydroxy-piperidin-1-yl-carbonyl)-quinazoline,
(179) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-ethoxycarbonyl-piperidin-1-yl-carbonyl]-quinazoline,
(180) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[1-(1,4,6,7-tetrahydro-pyrazolo[4,3]pyridin-5-yl)-carbonyl]-quinazoline,
(181) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(2R, 5S-dimethoxymethyl-pyrrolidin-1-yl-carbonyl)-quinazoline,
(182) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-methoxycarbonyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(183) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(pyrazolidin-1-yl-carbonyl)-quinazoline,
(184) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(1-oxo-thiomorpholin-4-yl-carbonyl)-quinazoline,
(185) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(2R/S)-2-[(N-butyl-N-ethyl-amino)-methyl]-piperidin-1-yl-carbonyl}-quinazoline,
(186) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[N-ethyl-N-(piperidin-4-yl)-aminocarbonyl]-quinazoline,
(187) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-ethoxycarbonyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(188) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-formyl-piperazin-1-yl-carbonyl)-quinazoline,
(189) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(2-dimethylamino-ethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(190) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(2-diethylamino-ethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(191) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl-carbonyl)-quinazoline,
(192) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(3,6-dihydro-2H-pyridin-1-yl-carbonyl)-quinazoline,
(193) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(2R/S)-2-[(N-butyl-N-methyl-amino)-methyl]-piperidin-1-yl-carbonyl}-quinazoline,
(194) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-methyl-morpholin-4-yl-carbonyl]-quinazoline,
(195) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(thiomorpholin-4-yl-carbonyl)-quinazoline,
(196) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(2-amino-ethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(197) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-ethyl-piperidin-1-yl-carbonyl]-quinazoline,
(198) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3R/S)-3-amino-pyrrolidin-1-yl-carbonyl]-quinazoline,
(199) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-trifluoromethyl-piperidin-1-yl-carbonyl)-quinazoline,
(200) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(3R/S)--[4-(pyrrolidin-1-yl)-butyl]-pyrrolidin-1-yl-carbonyl}-quinazoline,
(201) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(2R/S)-2-[(N-methyl-N-(pyridin-2-ylmethyl)-amino)-methyl]-piperidin-1-yl-carbonyl}-quinazoline,
(202) 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(4-hydroxy-piperazin-1-yl-carbonyl)-quinazoline,
(203) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(3R/S)-3-(pyrrolidin-1-ylmethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(204) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-diethylaminomethyl-piperidin-1-yl-carbonyl]-quinazoline,
(205) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(4-diethylamino-butyl)-piperidin-1-yl-carbonyl]-quinazoline,
(206) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R)-2-hydroxymethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(207) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(N-ethyl-N-methyl-aminomethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(208) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R)-2-aminocarbonyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(209) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2S)-2-hydroxymethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(210) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(4-methyl-piperazin-1-ylmethyl)-piperidin-1-yl-carbonyl]-quinazoline,
(211) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R)2-methoxymethyl-pyrrolidin-1-yl-carbonyl]-quinazoline,
(212) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(3-dimethylamino-propyl)-piperidin-1-yl-carbonyl]-quinazoline,
(213) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-diethylaminocarbonyl-piperidin-1-yl-carbonyl]-quinazoline,
(214) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(2R/S)-2-[(N-cyclohexyl-N-methyl-amino)-methyl]-piperidin-1-yl-carbonyl}-quinazoline, (215) 6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-piperidin-1-ylmethyl-piperidin-1-yl-carbonyl]-quinazoline,
(216) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(methylsulphanyl)-propylamino]-6-methoxy-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(217) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-6-methoxy-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(218) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2R/S)-2-(1-methyl-1H-pyrazol-4-yl)-thiazolidinyl-carbonyl]-quinazoline,
(219) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-7-(thiazolidinyl-carbonyl)-quinazoline,
(220) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-6-methyl-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(221) 4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-6-methyl-7-(thiazolidinyl-carbonyl)-quinazoline,
(222) 6-bromo-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(223) 6-bromo-4-[(1S)-1-(5-chloro-H-benzimidazol-2-yl)-2-methoxy-ethylamino]-7-(thiazolidinyl-carbonyl)-quinazoline,
(224) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-(6,7,8,9-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-4-yl)-quinazoline,
(225) 6-chloro-4-[(1S)-1-(5-chloro-1-methyl-1H-benzimidazol-2-yl)-3-methylsulphonylamino-propylamino]-7-(2,5-dihydropyrrolyl-carbonyl)-quinazoline,
(226) 6-chloro-4-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-benzyloxy-ethylamino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)- quinazoline,
(227) 6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[2-(pyridin-4-yl-amino)-ethylamino-carbonyl]-propylamino}-7- (pyrrolidin-1-yl-carbonyl)-quinazoline,
(228) 4-[(1S)-1-(5-bromo-1H-benzimidazol-2-yl)-2-methoxy-ethylamino]-6-chloro-7-(2,5-dihydropyrrolyl-carbonyl)-quinazoline,
(229) 4-[(1S)-1-(5-bromo-1H-benzimidazol-2-yl)-ethylamino]-6-chloro-7-(2,5-dihydropyrrolyl-carbonyl)-quinazoline,
(230) 6-bromo-4-[(1S)- 1 -(5-chloro-1H-benzimidazol-2-yl)-but-3-yn-1-yl-amino]-7-(2,5-dihydropyrrol-1-yl-carbonyl)-quinazoline,
(231) 4-[(1S,2R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-propylamino]-6-chloro-7-(2,5-dihydropyrrolyl-carbonyl)-quinazoline,
(232) 4-[(1S,2S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-tert.-butyloxy-propylamino]-6-chloro-7-(2,5-dihydropyrrolyl-carbonyl)-quinazoline, and
(233) 4-[(1S,2S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxy-propylamino]-6-chloro-7-(2,5-dihydropyrrolyl-carbonyl)-quinazoline.
3. A physiologically acceptable salt of the compound according to claim 1 .
4. A pharmaceutical composition comprising a compound according to claim 1 together with one or more inert carriers or diluents.Cited by (0)
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